메뉴 건너뛰기




Volumn , Issue 8, 2000, Pages 1497-1502

Synthesis of melithiazol B and related compounds via oxidative degradation of myxothiazol A and Z

Author keywords

Antibiotics; Melithiazol; Myxothiazol; Oxidations; Structure activity relationships; Thiazole

Indexed keywords

FUNGICIDE; MELITHIAZOL B; MYXOTHIAZOL A; MYXOTHIAZOL Z; UNCLASSIFIED DRUG;

EID: 0343569986     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200004)2000:8<1497::AID-EJOC1497>3.0.CO;2-8     Document Type: Article
Times cited : (14)

References (31)
  • 1
    • 0342679640 scopus 로고    scopus 로고
    • This work is part of the doctoral thesis of U. Söker, Technical University of Braunschweig, 1997. [1a] B. Böhlendorf, M. Herrmann, H.-J. Hecht, F. Sasse, E. Forche, H. Reichenbach, G. Höfle, Eur. J. Org. Chem. 1999, 2601-2608; F. Sasse, B. Böhlendorf, M. Herrmann, B. Kunze, E. Forche, H. Steinmetz, G. Höfle, H. Reichenbach, J. Antibiot. 1999, 52, 721-729. [1b] G. Höfle, in GBF Annual Report (Ed.: J.-H. Walsdorff), 1994, p. 133 and 1997, p. 97-98. [1c] G. Höfle, H. Reichenbach, B. Böhlendorf, F. Sasse (GBF), DE 94, 4410 449/WO 95/26414, 1995 (Chem. Abstr. 1996, 123, 339531).
    • (1999) Eur. J. Org. Chem. , pp. 2601-2608
    • Böhlendorf, B.1    Herrmann, M.2    Hecht, H.-J.3    Sasse, F.4    Forche, E.5    Reichenbach, H.6    Höfle, G.7
  • 2
    • 0345363099 scopus 로고    scopus 로고
    • This work is part of the doctoral thesis of U. Söker, Technical University of Braunschweig, 1997. [1a] B. Böhlendorf, M. Herrmann, H.-J. Hecht, F. Sasse, E. Forche, H. Reichenbach, G. Höfle, Eur. J. Org. Chem. 1999, 2601-2608; F. Sasse, B. Böhlendorf, M. Herrmann, B. Kunze, E. Forche, H. Steinmetz, G. Höfle, H. Reichenbach, J. Antibiot. 1999, 52, 721-729. [1b] G. Höfle, in GBF Annual Report (Ed.: J.-H. Walsdorff), 1994, p. 133 and 1997, p. 97-98. [1c] G. Höfle, H. Reichenbach, B. Böhlendorf, F. Sasse (GBF), DE 94, 4410 449/WO 95/26414, 1995 (Chem. Abstr. 1996, 123, 339531).
    • (1999) J. Antibiot. , vol.52 , pp. 721-729
    • Sasse, F.1    Böhlendorf, B.2    Herrmann, M.3    Kunze, B.4    Forche, E.5    Steinmetz, H.6    Höfle, G.7    Reichenbach, H.8
  • 3
    • 0345363099 scopus 로고    scopus 로고
    • (Ed.: J.-H. Walsdorff)
    • This work is part of the doctoral thesis of U. Söker, Technical University of Braunschweig, 1997. [1a] B. Böhlendorf, M. Herrmann, H.-J. Hecht, F. Sasse, E. Forche, H. Reichenbach, G. Höfle, Eur. J. Org. Chem. 1999, 2601-2608; F. Sasse, B. Böhlendorf, M. Herrmann, B. Kunze, E. Forche, H. Steinmetz, G. Höfle, H. Reichenbach, J. Antibiot. 1999, 52, 721-729. [1b] G. Höfle, in GBF Annual Report (Ed.: J.-H. Walsdorff), 1994, p. 133 and 1997, p. 97-98. [1c] G. Höfle, H. Reichenbach, B. Böhlendorf, F. Sasse (GBF), DE 94, 4410 449/WO 95/26414, 1995 (Chem. Abstr. 1996, 123, 339531).
    • (1994) GBF Annual Report , pp. 133
    • Höfle, G.1
  • 4
    • 0345363099 scopus 로고    scopus 로고
    • DE 94, 4410 449/WO 95/26414, 1995
    • This work is part of the doctoral thesis of U. Söker, Technical University of Braunschweig, 1997. [1a] B. Böhlendorf, M. Herrmann, H.-J. Hecht, F. Sasse, E. Forche, H. Reichenbach, G. Höfle, Eur. J. Org. Chem. 1999, 2601-2608; F. Sasse, B. Böhlendorf, M. Herrmann, B. Kunze, E. Forche, H. Steinmetz, G. Höfle, H. Reichenbach, J. Antibiot. 1999, 52, 721-729. [1b] G. Höfle, in GBF Annual Report (Ed.: J.-H. Walsdorff), 1994, p. 133 and 1997, p. 97-98. [1c] G. Höfle, H. Reichenbach, B. Böhlendorf, F. Sasse (GBF), DE 94, 4410 449/WO 95/26414, 1995 (Chem. Abstr. 1996, 123, 339531).
    • (1996) Chem. Abstr. , vol.123 , pp. 339531
    • Höfle, G.1    Reichenbach, H.2    Böhlendorf, B.3    Sasse, F.4
  • 12
    • 0001339060 scopus 로고    scopus 로고
    • For a recent review see e.g. H. Sauter, W. Steglich, T. Anke, Angew. Chem. 1999, 111, 1416-1438; Angew. Chem. Int. Ed. 1999, 38, 1328-1349.
    • (1999) Angew. Chem. , vol.111 , pp. 1416-1438
    • Sauter, H.1    Steglich, W.2    Anke, T.3
  • 13
    • 0033577815 scopus 로고    scopus 로고
    • For a recent review see e.g. H. Sauter, W. Steglich, T. Anke, Angew. Chem. 1999, 111, 1416-1438; Angew. Chem. Int. Ed. 1999, 38, 1328-1349.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1328-1349
  • 16
    • 0342614753 scopus 로고    scopus 로고
    • unpublished results
    • The ethyl and methyl imidates 6 have been prepared before and hydrolyzed under acidic conditions. The ethyl ester was isolated only in trace amounts: W. Trowitzsch-Kienast and B. Böhlendorf (GBF), unpublished results.
    • Trowitzsch-Kienast, W.1    Böhlendorf, B.2
  • 18
    • 25544441415 scopus 로고    scopus 로고
    • Doctoral Thesis, Technical University of Braunschweig
    • U. Söker, Doctoral Thesis, Technical University of Braunschweig, 1997.
    • (1997)
    • Söker, U.1
  • 20
    • 0343484785 scopus 로고    scopus 로고
    • unpublished results
    • N. Bedorf (GBF), unpublished results.
    • Bedorf, N.1
  • 21
    • 0000719844 scopus 로고
    • G. A. Russel, A. G. Bennis, J. Am. Chem. Soc. 1966, 83, 5491-5497; H. R. Gersmann, A. F. Bickel, J. Chem. Soc., (B) 1971, 2230-2237.
    • (1966) J. Am. Chem. Soc. , vol.83 , pp. 5491-5497
    • Russel, G.A.1    Bennis, A.G.2
  • 23
    • 0343484784 scopus 로고
    • (Houben-Weyl), Ed.: H. Kropf, 4th. ed.
    • A. de Meijere, F. Wolf, Methoden Org. Chem. (Houben-Weyl), Ed.: H. Kropf, 4th. ed. 1988, vol. E13, p. 985-990.
    • (1988) Methoden Org. Chem. , vol.E13 , pp. 985-990
    • De Meijere, A.1    Wolf, F.2
  • 24
    • 0343484781 scopus 로고
    • Alternatively the 14-carbanion could be oxidized by the hydroperoxide formed to give two molecules of alcohol 8, see e.g. M. F. Hawthorne, G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 2549-2551. However, this can be ruled out since addition of an excess of tert-butylhydroperoxide had no influence on the amount of alcohol 8 formed.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 2549-2551
    • Hawthorne, M.F.1    Hammond, G.S.2
  • 25
    • 0004164999 scopus 로고
    • (Ed.: W. Ando), Wiley
    • See e.g. N. A. Porter, in Organic Peroxides (Ed.: W. Ando), Wiley, 1992, p. 144.
    • (1992) Organic Peroxides , pp. 144
    • Porter, N.A.1
  • 27
    • 0343484782 scopus 로고    scopus 로고
    • This compound was also isolated from Archangium gephyra and named melithiazol M, see ref.[1]
    • This compound was also isolated from Archangium gephyra and named melithiazol M, see ref.[1]
  • 28
    • 4243272444 scopus 로고
    • Ed.: J.-H. Walsdorff
    • The compounds 12 and 15 have been isolated before in low yield from Myxococcus fulvus and named Myxothiazol O and N: G. Höfle, in GBF Annual Report (Ed.: J.-H. Walsdorff), 1986, p. 14-16.
    • (1986) GBF Annual Report , pp. 14-16
    • Höfle, G.1
  • 30
    • 0343484780 scopus 로고    scopus 로고
    • max(Δε) = 237 nm (+1.97). Due to a calculation error the wrong value of Δε = +2.8 was given in ref.[1a]
    • max(Δε) = 237 nm (+1.97). Due to a calculation error the wrong value of Δε = +2.8 was given in ref.[1a]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.